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Expedient five-step synthesis of SIB-1508Y from natural nicotine
被引:30
作者
:
Wagner, Florence F.
论文数:
0
引用数:
0
h-index:
0
机构:
N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
Wagner, Florence F.
[
1
]
Comins, Daniel L.
论文数:
0
引用数:
0
h-index:
0
机构:
N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
Comins, Daniel L.
[
1
]
机构
:
[1]
N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
来源
:
JOURNAL OF ORGANIC CHEMISTRY
|
2006年
/ 71卷
/ 22期
关键词
:
D O I
:
10.1021/jo0616052
中图分类号
:
O62 [有机化学];
学科分类号
:
070303 ;
081704 ;
摘要
:
Altinicline (SIB-1508Y), an anti-Parkinson's agent, was prepared in five steps from natural nicotine in 32% overall yield via a regioselective substitution of the pyridine ring of (S)-nicotine.
引用
收藏
页码:8673 / 8675
页数:3
相关论文
共 14 条
[1]
A practical and efficient synthesis of the selective neuronal acetylcholine-gated ion channel agonist (S)-(-)-5-ethynyl-3-(1-methyl-2-pyrrolidinyl)pyridine maleate (SIB-1508Y)
Bleicher, LS
论文数:
0
引用数:
0
h-index:
0
机构:
SIBA Neurosci Inc, La Jolla, CA 92037 USA
SIBA Neurosci Inc, La Jolla, CA 92037 USA
Bleicher, LS
Cosford, NDP
论文数:
0
引用数:
0
h-index:
0
机构:
SIBA Neurosci Inc, La Jolla, CA 92037 USA
SIBA Neurosci Inc, La Jolla, CA 92037 USA
Cosford, NDP
Herbaut, A
论文数:
0
引用数:
0
h-index:
0
机构:
SIBA Neurosci Inc, La Jolla, CA 92037 USA
SIBA Neurosci Inc, La Jolla, CA 92037 USA
Herbaut, A
McCallum, JS
论文数:
0
引用数:
0
h-index:
0
机构:
SIBA Neurosci Inc, La Jolla, CA 92037 USA
SIBA Neurosci Inc, La Jolla, CA 92037 USA
McCallum, JS
McDonald, IA
论文数:
0
引用数:
0
h-index:
0
机构:
SIBA Neurosci Inc, La Jolla, CA 92037 USA
SIBA Neurosci Inc, La Jolla, CA 92037 USA
McDonald, IA
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1998,
63
(04)
: 1109
-
1118
[2]
COMINS DL, Patent No. 7067672
[3]
COMINS DL, Patent No. 10925516
[4]
COMINS DL, Patent No. 60787116
[5]
CORNINS DL, 2006, TETRAHEDRON LETT, V47, P1449
[6]
Cosford N D, 2000, Pharm Acta Helv, V74, P125, DOI 10.1016/S0031-6865(99)00024-2
[7]
(S)-(-)-5-ethynyl-3-(1-methyl-2-pyrrolidinyl)pyridine Maleate (SIB-1508Y): A novel anti-Parkinsonian agent with selectivity for neuronal nicotinic acetylcholine receptors
Cosford, NDP
论文数:
0
引用数:
0
h-index:
0
机构:
SIBIA Neurosciences Inc., San Diego, CA 92037
Cosford, NDP
Bleicher, L
论文数:
0
引用数:
0
h-index:
0
机构:
SIBIA Neurosciences Inc., San Diego, CA 92037
Bleicher, L
Herbaut, A
论文数:
0
引用数:
0
h-index:
0
机构:
SIBIA Neurosciences Inc., San Diego, CA 92037
Herbaut, A
McCallum, JS
论文数:
0
引用数:
0
h-index:
0
机构:
SIBIA Neurosciences Inc., San Diego, CA 92037
McCallum, JS
Vernier, JM
论文数:
0
引用数:
0
h-index:
0
机构:
SIBIA Neurosciences Inc., San Diego, CA 92037
Vernier, JM
Dawson, H
论文数:
0
引用数:
0
h-index:
0
机构:
SIBIA Neurosciences Inc., San Diego, CA 92037
Dawson, H
Whitten, JP
论文数:
0
引用数:
0
h-index:
0
机构:
SIBIA Neurosciences Inc., San Diego, CA 92037
Whitten, JP
Adams, P
论文数:
0
引用数:
0
h-index:
0
机构:
SIBIA Neurosciences Inc., San Diego, CA 92037
Adams, P
ChavezNoriega, L
论文数:
0
引用数:
0
h-index:
0
机构:
SIBIA Neurosciences Inc., San Diego, CA 92037
ChavezNoriega, L
Correa, LD
论文数:
0
引用数:
0
h-index:
0
机构:
SIBIA Neurosciences Inc., San Diego, CA 92037
Correa, LD
Crona, JH
论文数:
0
引用数:
0
h-index:
0
机构:
SIBIA Neurosciences Inc., San Diego, CA 92037
Crona, JH
Mahaffy, LS
论文数:
0
引用数:
0
h-index:
0
机构:
SIBIA Neurosciences Inc., San Diego, CA 92037
Mahaffy, LS
Menzaghi, F
论文数:
0
引用数:
0
h-index:
0
机构:
SIBIA Neurosciences Inc., San Diego, CA 92037
Menzaghi, F
Rao, TS
论文数:
0
引用数:
0
h-index:
0
机构:
SIBIA Neurosciences Inc., San Diego, CA 92037
Rao, TS
Reid, R
论文数:
0
引用数:
0
h-index:
0
机构:
SIBIA Neurosciences Inc., San Diego, CA 92037
Reid, R
Sacaan, AI
论文数:
0
引用数:
0
h-index:
0
机构:
SIBIA Neurosciences Inc., San Diego, CA 92037
Sacaan, AI
Santori, E
论文数:
0
引用数:
0
h-index:
0
机构:
SIBIA Neurosciences Inc., San Diego, CA 92037
Santori, E
Stauderman, KA
论文数:
0
引用数:
0
h-index:
0
机构:
SIBIA Neurosciences Inc., San Diego, CA 92037
Stauderman, KA
Whelan, K
论文数:
0
引用数:
0
h-index:
0
机构:
SIBIA Neurosciences Inc., San Diego, CA 92037
Whelan, K
Lloyd, GK
论文数:
0
引用数:
0
h-index:
0
机构:
SIBIA Neurosciences Inc., San Diego, CA 92037
Lloyd, GK
McDonald, IA
论文数:
0
引用数:
0
h-index:
0
机构:
SIBIA Neurosciences Inc., San Diego, CA 92037
McDonald, IA
[J].
JOURNAL OF MEDICINAL CHEMISTRY,
1996,
39
(17)
: 3235
-
3237
[8]
Enantioselective reduction of heteroaromatic β,γ-unsaturated ketones as an alternative to allylboration of aldehydes.: Application:: asymmetric synthesis of SIB-1508Y
Felpin, FX
论文数:
0
引用数:
0
h-index:
0
机构:
Fac Sci & Tech, Synth Organ Lab, CNRS, UMR 6513, F-44322 Nantes 3, France
Fac Sci & Tech, Synth Organ Lab, CNRS, UMR 6513, F-44322 Nantes 3, France
Felpin, FX
Bertrand, MJ
论文数:
0
引用数:
0
h-index:
0
机构:
Fac Sci & Tech, Synth Organ Lab, CNRS, UMR 6513, F-44322 Nantes 3, France
Fac Sci & Tech, Synth Organ Lab, CNRS, UMR 6513, F-44322 Nantes 3, France
Bertrand, MJ
Lebreton, J
论文数:
0
引用数:
0
h-index:
0
机构:
Fac Sci & Tech, Synth Organ Lab, CNRS, UMR 6513, F-44322 Nantes 3, France
Fac Sci & Tech, Synth Organ Lab, CNRS, UMR 6513, F-44322 Nantes 3, France
Lebreton, J
[J].
TETRAHEDRON,
2002,
58
(37)
: 7381
-
7389
[9]
The first enantioselective synthesis of (S)-5-bromo-3-(1-methyl-2-pyrrolidinyl)pyridine:: a key intermediate for the preparation of SIB-1508Y
Felpin, FX
论文数:
0
引用数:
0
h-index:
0
机构:
Fac Sci & Tech, CNRS, UMR 6513, Organ Synth Lab, F-44322 Nantes 3, France
Fac Sci & Tech, CNRS, UMR 6513, Organ Synth Lab, F-44322 Nantes 3, France
Felpin, FX
Vo-Thanh, G
论文数:
0
引用数:
0
h-index:
0
机构:
Fac Sci & Tech, CNRS, UMR 6513, Organ Synth Lab, F-44322 Nantes 3, France
Fac Sci & Tech, CNRS, UMR 6513, Organ Synth Lab, F-44322 Nantes 3, France
Vo-Thanh, G
Villiéras, J
论文数:
0
引用数:
0
h-index:
0
机构:
Fac Sci & Tech, CNRS, UMR 6513, Organ Synth Lab, F-44322 Nantes 3, France
Fac Sci & Tech, CNRS, UMR 6513, Organ Synth Lab, F-44322 Nantes 3, France
Villiéras, J
Lebreton, J
论文数:
0
引用数:
0
h-index:
0
机构:
Fac Sci & Tech, CNRS, UMR 6513, Organ Synth Lab, F-44322 Nantes 3, France
Fac Sci & Tech, CNRS, UMR 6513, Organ Synth Lab, F-44322 Nantes 3, France
Lebreton, J
[J].
TETRAHEDRON-ASYMMETRY,
2001,
12
(08)
: 1121
-
1124
[10]
Regioselective C-2 and C-6 substitution of (S)-nicotine and nicotine derivatives
Février, FC
论文数:
0
引用数:
0
h-index:
0
机构:
N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
Février, FC
Smith, ED
论文数:
0
引用数:
0
h-index:
0
机构:
N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
Smith, ED
Comins, DL
论文数:
0
引用数:
0
h-index:
0
机构:
N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
Comins, DL
[J].
ORGANIC LETTERS,
2005,
7
(24)
: 5457
-
5460
←
1
2
→
共 14 条
[1]
A practical and efficient synthesis of the selective neuronal acetylcholine-gated ion channel agonist (S)-(-)-5-ethynyl-3-(1-methyl-2-pyrrolidinyl)pyridine maleate (SIB-1508Y)
Bleicher, LS
论文数:
0
引用数:
0
h-index:
0
机构:
SIBA Neurosci Inc, La Jolla, CA 92037 USA
SIBA Neurosci Inc, La Jolla, CA 92037 USA
Bleicher, LS
Cosford, NDP
论文数:
0
引用数:
0
h-index:
0
机构:
SIBA Neurosci Inc, La Jolla, CA 92037 USA
SIBA Neurosci Inc, La Jolla, CA 92037 USA
Cosford, NDP
Herbaut, A
论文数:
0
引用数:
0
h-index:
0
机构:
SIBA Neurosci Inc, La Jolla, CA 92037 USA
SIBA Neurosci Inc, La Jolla, CA 92037 USA
Herbaut, A
McCallum, JS
论文数:
0
引用数:
0
h-index:
0
机构:
SIBA Neurosci Inc, La Jolla, CA 92037 USA
SIBA Neurosci Inc, La Jolla, CA 92037 USA
McCallum, JS
McDonald, IA
论文数:
0
引用数:
0
h-index:
0
机构:
SIBA Neurosci Inc, La Jolla, CA 92037 USA
SIBA Neurosci Inc, La Jolla, CA 92037 USA
McDonald, IA
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1998,
63
(04)
: 1109
-
1118
[2]
COMINS DL, Patent No. 7067672
[3]
COMINS DL, Patent No. 10925516
[4]
COMINS DL, Patent No. 60787116
[5]
CORNINS DL, 2006, TETRAHEDRON LETT, V47, P1449
[6]
Cosford N D, 2000, Pharm Acta Helv, V74, P125, DOI 10.1016/S0031-6865(99)00024-2
[7]
(S)-(-)-5-ethynyl-3-(1-methyl-2-pyrrolidinyl)pyridine Maleate (SIB-1508Y): A novel anti-Parkinsonian agent with selectivity for neuronal nicotinic acetylcholine receptors
Cosford, NDP
论文数:
0
引用数:
0
h-index:
0
机构:
SIBIA Neurosciences Inc., San Diego, CA 92037
Cosford, NDP
Bleicher, L
论文数:
0
引用数:
0
h-index:
0
机构:
SIBIA Neurosciences Inc., San Diego, CA 92037
Bleicher, L
Herbaut, A
论文数:
0
引用数:
0
h-index:
0
机构:
SIBIA Neurosciences Inc., San Diego, CA 92037
Herbaut, A
McCallum, JS
论文数:
0
引用数:
0
h-index:
0
机构:
SIBIA Neurosciences Inc., San Diego, CA 92037
McCallum, JS
Vernier, JM
论文数:
0
引用数:
0
h-index:
0
机构:
SIBIA Neurosciences Inc., San Diego, CA 92037
Vernier, JM
Dawson, H
论文数:
0
引用数:
0
h-index:
0
机构:
SIBIA Neurosciences Inc., San Diego, CA 92037
Dawson, H
Whitten, JP
论文数:
0
引用数:
0
h-index:
0
机构:
SIBIA Neurosciences Inc., San Diego, CA 92037
Whitten, JP
Adams, P
论文数:
0
引用数:
0
h-index:
0
机构:
SIBIA Neurosciences Inc., San Diego, CA 92037
Adams, P
ChavezNoriega, L
论文数:
0
引用数:
0
h-index:
0
机构:
SIBIA Neurosciences Inc., San Diego, CA 92037
ChavezNoriega, L
Correa, LD
论文数:
0
引用数:
0
h-index:
0
机构:
SIBIA Neurosciences Inc., San Diego, CA 92037
Correa, LD
Crona, JH
论文数:
0
引用数:
0
h-index:
0
机构:
SIBIA Neurosciences Inc., San Diego, CA 92037
Crona, JH
Mahaffy, LS
论文数:
0
引用数:
0
h-index:
0
机构:
SIBIA Neurosciences Inc., San Diego, CA 92037
Mahaffy, LS
Menzaghi, F
论文数:
0
引用数:
0
h-index:
0
机构:
SIBIA Neurosciences Inc., San Diego, CA 92037
Menzaghi, F
Rao, TS
论文数:
0
引用数:
0
h-index:
0
机构:
SIBIA Neurosciences Inc., San Diego, CA 92037
Rao, TS
Reid, R
论文数:
0
引用数:
0
h-index:
0
机构:
SIBIA Neurosciences Inc., San Diego, CA 92037
Reid, R
Sacaan, AI
论文数:
0
引用数:
0
h-index:
0
机构:
SIBIA Neurosciences Inc., San Diego, CA 92037
Sacaan, AI
Santori, E
论文数:
0
引用数:
0
h-index:
0
机构:
SIBIA Neurosciences Inc., San Diego, CA 92037
Santori, E
Stauderman, KA
论文数:
0
引用数:
0
h-index:
0
机构:
SIBIA Neurosciences Inc., San Diego, CA 92037
Stauderman, KA
Whelan, K
论文数:
0
引用数:
0
h-index:
0
机构:
SIBIA Neurosciences Inc., San Diego, CA 92037
Whelan, K
Lloyd, GK
论文数:
0
引用数:
0
h-index:
0
机构:
SIBIA Neurosciences Inc., San Diego, CA 92037
Lloyd, GK
McDonald, IA
论文数:
0
引用数:
0
h-index:
0
机构:
SIBIA Neurosciences Inc., San Diego, CA 92037
McDonald, IA
[J].
JOURNAL OF MEDICINAL CHEMISTRY,
1996,
39
(17)
: 3235
-
3237
[8]
Enantioselective reduction of heteroaromatic β,γ-unsaturated ketones as an alternative to allylboration of aldehydes.: Application:: asymmetric synthesis of SIB-1508Y
Felpin, FX
论文数:
0
引用数:
0
h-index:
0
机构:
Fac Sci & Tech, Synth Organ Lab, CNRS, UMR 6513, F-44322 Nantes 3, France
Fac Sci & Tech, Synth Organ Lab, CNRS, UMR 6513, F-44322 Nantes 3, France
Felpin, FX
Bertrand, MJ
论文数:
0
引用数:
0
h-index:
0
机构:
Fac Sci & Tech, Synth Organ Lab, CNRS, UMR 6513, F-44322 Nantes 3, France
Fac Sci & Tech, Synth Organ Lab, CNRS, UMR 6513, F-44322 Nantes 3, France
Bertrand, MJ
Lebreton, J
论文数:
0
引用数:
0
h-index:
0
机构:
Fac Sci & Tech, Synth Organ Lab, CNRS, UMR 6513, F-44322 Nantes 3, France
Fac Sci & Tech, Synth Organ Lab, CNRS, UMR 6513, F-44322 Nantes 3, France
Lebreton, J
[J].
TETRAHEDRON,
2002,
58
(37)
: 7381
-
7389
[9]
The first enantioselective synthesis of (S)-5-bromo-3-(1-methyl-2-pyrrolidinyl)pyridine:: a key intermediate for the preparation of SIB-1508Y
Felpin, FX
论文数:
0
引用数:
0
h-index:
0
机构:
Fac Sci & Tech, CNRS, UMR 6513, Organ Synth Lab, F-44322 Nantes 3, France
Fac Sci & Tech, CNRS, UMR 6513, Organ Synth Lab, F-44322 Nantes 3, France
Felpin, FX
Vo-Thanh, G
论文数:
0
引用数:
0
h-index:
0
机构:
Fac Sci & Tech, CNRS, UMR 6513, Organ Synth Lab, F-44322 Nantes 3, France
Fac Sci & Tech, CNRS, UMR 6513, Organ Synth Lab, F-44322 Nantes 3, France
Vo-Thanh, G
Villiéras, J
论文数:
0
引用数:
0
h-index:
0
机构:
Fac Sci & Tech, CNRS, UMR 6513, Organ Synth Lab, F-44322 Nantes 3, France
Fac Sci & Tech, CNRS, UMR 6513, Organ Synth Lab, F-44322 Nantes 3, France
Villiéras, J
Lebreton, J
论文数:
0
引用数:
0
h-index:
0
机构:
Fac Sci & Tech, CNRS, UMR 6513, Organ Synth Lab, F-44322 Nantes 3, France
Fac Sci & Tech, CNRS, UMR 6513, Organ Synth Lab, F-44322 Nantes 3, France
Lebreton, J
[J].
TETRAHEDRON-ASYMMETRY,
2001,
12
(08)
: 1121
-
1124
[10]
Regioselective C-2 and C-6 substitution of (S)-nicotine and nicotine derivatives
Février, FC
论文数:
0
引用数:
0
h-index:
0
机构:
N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
Février, FC
Smith, ED
论文数:
0
引用数:
0
h-index:
0
机构:
N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
Smith, ED
Comins, DL
论文数:
0
引用数:
0
h-index:
0
机构:
N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
Comins, DL
[J].
ORGANIC LETTERS,
2005,
7
(24)
: 5457
-
5460
←
1
2
→